Abstract：
In keeping with our investigation, a simple and practical synthesis of novel heterocyclic compounds with a sulfamoyl moiety that can be employed as insecticidal agents was reported. The compound 2-hydrazinyl-N-(4-sulfamoylphenyl)-2-thioxoacetamide 1 was coupled smoothly with triethylorthoformate or a variety of halo compounds, namely phenacyl chloride, chloroacetyl chloride, chloroacetaldehyde, chloroacetone, 1,3-dichloropropane, 1,2-dichloroethane, ethyl chloroformate, 2,3-dichloro-1,4-naphthoquinone, and chloroanil respectively, which afforded the 1,3,4-thiadiazole and 1,3,4-thiadiazine derivatives. The new products structure was determined using elemental and spectral analysis. Under laboratory conditions, the biological and toxicological effects of the synthetic compounds were also evaluated as insecticides against Spodoptera littoralis (Boisd.). Compounds 3 and 5 had LC50 values of 6.42 and 6.90 mg/L, respectively. The investigated compounds (from 2 to 11) had been undergoing molecular docking investigation for prediction of the optimal arrangement and strength of binding between the ligand (herein, the investigated compounds (from 2 to 11)) and a receptor (herein, the 2CH5) molecule. The binding affinity within docking score (S, kcal/mol) ranged between -8.23 (for compound 5), -8.12 (for compound 3) and -8.03 (for compound 9) to -6.01 (for compound 8). These compounds were shown to have a variety of binding interactions within the 2CH5 active site, as evidenced by protein-ligand docking configurations. This study gives evidence that those compounds have 2CH5-inhibitory capabilities and hence may be used for 2CH5-targeting development. Furthermore, the three top-ranked compounds (5, 3, and 9) and the standard buprofezin were subjected to density functional theory (DFT) analysis. The highest occupied molecular orbital-lowest unoccupied molecular orbital (HOMO-LUMO) energy difference (ΔE) of compounds 5, 3, and 9 was found to be comparable to that of buprofezin. These findings highlighted the potential and relevance of charge transfer at the molecular level.
摘要：
根据我们的调查，报道了可以用作杀虫剂的具有氨磺酰基部分的新型杂环化合物的简单实用的合成。化合物2-肼基-N-（4-氨磺酰基苯基）-2-硫代乙酰胺1与原甲酸三乙酯或多种卤代化合物顺利偶联，即苯甲酰氯，氯乙酰氯,氯乙醛,氯丙酮,1,3-二氯丙烷,1,2-二氯乙烷,氯甲酸乙酯,2,3-二氯-1,4-萘醌,分别为氯茴香，得到1,3,4-噻二唑和1,3,4-噻二嗪衍生物。使用元素和光谱分析确定了新产品的结构。在实验室条件下,合成化合物的生物和毒理学作用也被评估为杀虫剂对斜纹夜蛾（Boisd。).化合物3和5的LC50值为6.42和6.90mg/L,分别。所研究的化合物（从2到11）一直在进行分子对接研究，以预测配体之间的最佳排列和结合强度（本文，所研究的化合物(从2到11))和受体(本文，2CH5)分子。对接得分内的结合亲和力(S，千卡/摩尔)范围在-8.23之间(对于化合物5)，-8.12(对于化合物3)和-8.03(对于化合物9)至-6.01(对于化合物8)。这些化合物显示在2CH5活性位点内具有多种结合相互作用，蛋白质-配体对接构型证明了这一点。该研究提供了这些化合物具有2CH5抑制能力的证据,因此可用于2CH5靶向开发。此外，对三个排序最高的化合物(5、3和9)和标准的Buprofezin进行密度泛函理论(DFT)分析。发现化合物5、3和9的最高占据分子轨道-最低未占据分子轨道（HOMO-LUMO）能差（ΔE）与buprofezin相当。这些发现强调了分子水平上电荷转移的潜力和相关性。
